L-Serine → N-[(1,1-Dimethylethoxy)carbonyl]-L-phenylalanyl-L-serine

HRID 427358Notes

Reaction equation

HRID 427358 reaction equation
CN(C=O)C.[NH:6]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:7]([C:15]([O:17]N1C(=O)CCC1=O)=O)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH2:32][C@H:33]([C:36]([OH:38])=[O:37])[CH2:34][OH:35].CCN(CC)CC>>[NH:6]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[C@H:7]([C:15]([NH:32][C@H:33]([C:36]([OH:38])=[O:37])[CH2:34][OH:35])=[O:17])[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 4

HCID 5951L-Serine2×HCID 6228DimethylformamideHCID 8471Triethylamine2×HCID 107447tert-Butyl (S)-(1-benzyl-2-((2,5-dioxo-1-pyrrolidinyl)oxy)-2-oxoethyl)carbamate

Product 1

HCID 13892838N-[(1,1-Dimethylethoxy)carbonyl]-L-phenylalanyl-L-serineYield 31%

Procedure

In a 10 ml solution of DMF containing 500 mg (1.38 mmol) of Boc-Phe-OSu was added 5 ml of an aqueous solution of H-Ser-OH.Et3N [preparation from 290 mg (2.76 mmol) of H-Ser-OH and 384 μl (2.76 mmol) of Et3N] and the mixture was stirred for 14 hr. The reaction mixture was evaporated and the residue was dissolved in ethyl acetate and washed with 1N-HCl and saturated sodium chloride aqueous solution, successively, together with salting out. The resultant solution was dried over anhydrous sodium sulfate, evaporated under reduced pressure, and the resulting residue was purified with a silica gel column chromatography (CHCl3:MeOH). The eluate was mixed with ether and n-hexane to give crystals of 150 mg of the title compound with yield of 31%.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with 1N-HCl and saturated sodium chloride aqueous solution
  4. dry with materialThe resultant solution was dried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customthe resulting residue was purified with a silica gel column chromatography (CHCl3:MeOH)
  7. additionThe eluate was mixed with ether and n-hexane

Sources & evidence

ORD record
ord-2a5ac6d0db8e447eb457f63bfb7b82ea
Source dataset
uspto-grants-2001_11
Patent number
US06313094B1

Reaction notes

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